Western Massachusetts Fall Roadtrip, Full of Hidden Gems

Massachusetts Fall Foliage Road Trip

Each year thousands of leaf peepers tumble into their cars and head north toward the mountains of Maine, New Hampshire and Vermont to be dazzled by fall foliage displays.  Highways become clogged, restaurants are filled to overflowing, hotels are sold out and prices are at their max.

This year we have a smarter suggestion for you, instead of heading north, point your car toward Western Massachusetts and discover the beauty of ancestral farms, hillsides awash with fall colors and small towns chock full of farm stands, art, music, history and artisan craft shops.  Fall foliage is just as brilliant in this verdant region, but you’ll miss the annoying crowds.

Massachusetts Fall Foliage Road Trip

Stop One – Northampton, Massachusetts

Less than a two hour drive west of Boston heading out along the Mass Pike, (1 hr from Hartford, CT) our first stop is the charming young-at-heart city of Northampton, Massachusetts.  Since the 1600’s this area has been known as the “Paradise of America”, and residents today will tell you that the utopian nature of their city shines on.  Northampton enjoys the enthusiastic influence of 5 nearby colleges; Smith, Mount Holyoke, Amherst, Hampshire and the University of Massachusetts.

Northampton Massachusetts

True to many college towns, Northampton has long been a magnet for arts, music and cultural expressions of all description.  The downtown of this 350 year old community is graced by stately turn-of-the-century architecture and is bordered by the lush campus of Smith College.  A lively Main Street is dotted with an eclectic variety of mom-and-pop shops and intriguing restaurants.  Here are just some of the interesting sites of Northampton that will easily entertain you for the day.

  • Calvin Coolidge casts a large shadow here as he was Mayor of Northampton before becoming the 30th President of The United States.  Visit the Coolidge homestead, Presidential Library housed in the Forbes Library, and the Calvin Theater which still attracts top flight performers.Forbes Library Northampton MA
  • Stroll through the Smith College Botanic Gardens and visit their themed gardens and handsome Victorian conservatory with thousands of plants on display.
  • Northampton is home to over a dozen art galleries displaying everything from traditional paintings to local crafts that will amaze you or perhaps tickle your funny bone.
  • Plan to attend a performance in one of Northampton’s six theaters, being sure to visit the Academy of Music and Calvin Theater.
  • Northampton is the epicenter for Gypsy Jazz and the music of Django Reinhardt.  Each summer the Academy of Music hosts the Gypsy Jazz Festival with top Django performers.  Learn about this jazz movement and pick up some music in local shops.

Thornes Marketplace Northampton

  • Wander along “Shop Row” with it’s far-out blend of traditional wares and free-spirited shops that will make you think you’ve returned to the 60s!  Don’t miss a stop at Thornes Marketplace where you’ll find a former department store which now houses dozens of boutiques.  Our favorite merchants are Heavenly Chocolate and Herrells Ice Cream where you’re likely to find a line at most hours of the day – yes, the ice cream is that good!
  • Don’t miss seeing the mural, History of Women in Northampton, located on Mechanic Street.
  • This is best place to tune up your yo-yo skills.  Each summer they host the Northeast and Massachusetts YoYo Championships, and you’ll find lots of yo-yo themed goods in local stores.
  • Summer and Fall brings an abundance of local ingredients and produce to street markets on weekends through mid-November.
  • Bring along your bikes and ride the network of  Rail Tails between Northampton and Easthampton.

Walking Tours – Stop by the Visitor’s Center at 99 Pleasant Street and pick up a brochure of 6 self-guided walking tours.  For a more personalized and enlightening experience, take a walking tour with expert guide, Zane Lumelsky.  Zane led us through the streets of Northampton revealing fascinating history, architecture, local customs and noted personalities.  Anyone planning to attend one of the area colleges should definitely take a tour with Zane.  Give him a call at (413) 210-0740 or email at [email protected] and he will tailor a walking tour for your particular interests.

Where To Stay and Dine
Hotel Northampton MA
Image By AlexiusHoratius

The historic Hotel Northampton located right on King Street is really the only choice in my mind.  It is located right in the center of all the action, priced affordably, and is an exceptional hotel experience.  Rooms are roomy and decorated with a nod to its New England heritage.  The lobby restaurant and bar are bright and cheery, and the sunny patio is a wonderful spot for an afternoon cocktail to rest your tired feet.  A meal in the historic Wiggins Tavern is a special treat as this rustic tavern makes you feel like you’ve traveled back to the 1700’s.  In town we loved The Eastside Grill.  The waitstaff was terrific and our seafood dinners were so fresh and delicious we’d swear we were at the shore.

Stop Two – Quabbin Reservoir (Optional)

If you’ve always wondered just where your drinking water comes from, the Quabbin Reservoir makes a fascinating and scenic side trip.  Located about an hour drive to the northeast, the Quabbin Reservoir supplies drinking water to most of eastern Massachusetts.  The Visitor Center is located at 485 Ware Road (Rte 9) in Belchertown, MA.

While you’re traveling Route 9, a MUST stop is The Roadhouse Cafe in Belchertown.  Oh my goodness, the food is sensational!  From breads to jams and everything in-between, it’s all homemade and organic.  We met the friendly owners, Mike and Deb who pour their love into this cute roadside restaurant that’s open for breakfast and lunch.  I would gladly drive a few extra country miles for a slice of Deb’s homemade breads!

Stop Three – Shop Til-You-Drop at the Yankee Candle Flagship Store in South Deerfield

Yankee Candle Flagship Store

This store is so large, it’s practically a village, and it’s WAY more than a candle shop.  Yes, you’ll find candles of every size, color and scent (you can even make your own design), but there are also more household decorative items than you’ve ever seen in your life.  You’ll find decor for the kitchen, the man cave, the patio, upcoming holidays and something for every surface of your home.  And yes, there are lots of benches for your husband to take a time-out, although you may find him in the Harley section.

Stop Four – The Historic Colonial Village of Deerfield

Heading a bit further north on Route 24 will bring you to the beautiful colonial village of Historic Deerfield.  Making your way down Old Main Street, you will think that it was surely designed with the fall foliage season in mind.  Stately maples stretch their branches wide creating arches over streets and sidewalks.  The effect of arched colors begs to be photographed and kept as a favorite fall memory.

Deerfield MA in Fall Foliage Season

You could easily spend days exploring the homesteads, schools and working farms of Historic Deerfield. This non-profit preservation organization, has preserved, restored and recreated a farming town of early New England.  Historic Deerfield is a living museum with more than 15 preserved buildings and homes that tell the story of life in the Pioneer Valley from the town’s founding in 1677 to prosperous farming day in the 1800s.  What makes this experience exceptional, is the tales of the area’s families that have been preserved along with the buildings.  Life was not always picture perfect in this valley and you’ll see the struggles and successes they faced in their lives.  Stop into the visitor center to watch the video of early life in the valley and to purchase your tickets to tour the historic homes.

Historic Deerfield Village

During the fall season there are lots of events and exhibitions throughout the village.  The Historic Deerfield Antiques Show over Columbus Day Weekend draws antiques enthusiasts from surrounding states.  You’ll also find demonstrations of weaving, hearth cooking, basket making, woodworking, blacksmithing, coopering and lots more throughout the village.

Where To Stay – Deerfield Inn

Deerfield Inn

The Deerfield Inn at the heart of Old Main Street and across from the visitor’s center is totally charming.  Sit and have tea in the sunny livingroom or enjoy a cocktail at the tavern.  Chapney’s Restaurant serves three meals a day and is a great gathering spot for travelers and locals alike.  The menu reflects the abundance of produce from local farms. Rooms are lovingly decorated with period pieces and there are accommodations for families as well.  You will likely meet innkeepers Jane and Karl, as they are front and center to assure that you have having a wonderful stay.  Advance reservations are essential as this inn has been in demand from the days of stagecoach travel right up to today.

You’ll hate to leave this charming village, but the road home awaits along Route 2.  You’ll pass lots of farm stands and pick-your-own apple orchards as you make your way east.  Pick up your Halloween pumpkin to remind yourself of the wonderful foliage visit you’ve had to beautiful Western Massachusetts.

Image Source:  WickedGoodTravelTips.com, Hotel Northampton, Deerfield Inn

Thank you to the Hampshire County Regional Tourism Council for hosting our visit to Hampshire County.  Visit their website as they are a great resource for planning your trip.


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